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Ben Cherington’s Worst Moves as Pirates’ GM



Pittsburgh Pirates, Ben Cherington

After examining the best moves he’s made since taking over as general manager for the Pittsburgh Pirates, it’s time to break down the moves Ben Cherington has made that haven’t gone to plan.

As is the case with any GM across the league, there are some trades that work out and some that don’t. Trades will be much of the focus here.

For the most part, it’s still too early to judge the returns on draft selections made in the four years under Cherington. Still, there are at least some questions to be raised about first-rounders Nick Gonzales (2020) and Henry Davis (2021) after both made their major-league debuts last season.

Of what is already easier to judge, here are some deals that Cherington regrets.


In 2021, the Pirates sent right-handed reliever Clay Holmes to the New York Yankees for infield prospects Hoy Park and Diego Castillo.

At the time, it looked more like a win for Ben Cherington and the Pirates. Holmes showed good stuff during his time with the Pirates, but it didn’t necessarily translate to strong results.

Park and Castillo, though neither established themselves as big leaguers, had solid track records as they rose through the minor-league ranks.

The two infielders combined for only 163 games with the Pirates and posted well below-par numbers at the plate. Neither Park nor Castillo are still in the organization after being designated for assignment.

Holmes, meanwhile, has carved out a role as the Yankees closer and was an All-Star in 2022. In 153 appearances during his tenure in New York, he has a 2.50 ERA to go along with 44 saves.


This past June, the Pirates dealt reliever Robert Stephenson to the Tampa Bay Rays for infield prospect Alika Williams.

Williams possesses a strong glove at shortstop, but he’s limited offensively. The 24-year-old played in 46 games with the Pirates in his debut season in 2023. He finished the year under the Mendoza line with a .198 batting average, which was paired with a .518 OPS and zero home runs.

After the trade, Stephenson transformed into one of the more dominant relievers in baseball. The right-hander totaled 38.1 innings pitched with the Rays across 42 appearances. He pitched to a 2.35 ERA and struck out 60 batters while holding opponents to a .138 batting average against.

This offseason, Stephenson signed a three-year, $33 million deal with the Los Angeles Angels.


On Christmas Eve in 2020, Ben Cherington executed one of the first significant deals since he took over the reigns. The Pirates traded first baseman Josh Bell to the Washington Nationals for a pair of right-handed pitchers — Wil Crowe and Eddy Yean.

The Pirates sold low on Bell, who struggled during the pandemic-shortened 2020 season. Though he’s somewhat limited as a bat-only profile, Bell has turned into a steady contributor at the plate.

Since the trade, Bell has slashed .258/.345/.438 with 66 home runs and 233 RBIs in 450 games.

For the Pirates, Crowe was initially utilized as a starting pitcher before transitioning to a bullpen role. He was never able to find a groove and was DFA’d by the club in 2023. Yean spent last season in High-A, where he finished with a 5.01 ERA in 40 appearances.


The Pirates are never going to spend at the levels of the big-market clubs. Even with that being true, a number of the free agent signings under Ben Cherington have been underwhelming.

Some of the uninspiring signings that have not panned out in Pittsburgh include — Luke Maile, Guillermo Heredia, Jarrod Dyson, JT Riddle, Trevor Cahill, Yoshi Tsutsugo (re-signed), Heath Hembree, Andrew Knapp, Jake Marisnick and Austin Hedges.

Also of note, the Pirates still have yet to sign a free agent to a multi-year agreement under Cherington. The largest contract given to a player on the open market is Aroldis Chapman’s $10.5 million for the 2024 season.

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